I said yes. Ive been involved in a $50 redraft league for the last several years with guys i dont know besides being on the cafe. It is far and away my best league. I have not had any problems with it.
That said 2 years ago i participated in a money league with a Cafe Vet (Nebbie) and he stiffed the winners of the league.
Money leagues with strangers is risky but if you're smart about it theres not as much risk as you would think. I ALWAYS use paypal when sending money to someone i dont personally know. That way if they do stiff me i can at least send a complaint to paypal and they will freeze the persons account. Not a 100% gurantee but its defintely a deterent.

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